Sodium Bisulfite → 2-[(1,2-Dichloroethenyl)oxy]benzene-1-sulfonamide

HRID 985892Notes

Reaction equation

HRID 985892 reaction equation
N[C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[O:4][C:5]([Cl:8])=[CH:6][Cl:7].[N:13]([O-])=O.[Na+].[S:17](=[O:20])(O)[O-:18].[Na+]>C(O)(=O)C.Cl.O.S([O-])([O-])(=O)=O.[Cu+2]>[Cl:8][C:5]([O:4][C:3]1[CH:9]=[CH:10][CH:11]=[CH:12][C:2]=1[S:17]([NH2:13])(=[O:20])=[O:18])=[CH:6][Cl:7]

Participants

8

Reactant 3

HCID 23665763Sodium BisulfiteHCID 23668193Sodium NitriteHCID 543384152-[(1,2-Dichloroethenyl)oxy]aniline

Product 1

HCID 537128512-[(1,2-Dichloroethenyl)oxy]benzene-1-sulfonamide

Reagents, catalysts & solvents 4

HCID 24462Copper SulfateCatalystHCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent2×

Procedure

Twenty four grams of 1-(2-aminophenoxy)-1,2-dichloroethene was dissolved in a mixture of 25 ml acetic acid, 25 ml of 12N hydrochloric acid and 50 ml of water. The grown mixture was cooled to 0° and a solution of 8.28 g of sodium nitrite in 15 ml of water was added dropwise. The resulting brown suspension was stirred at below 5° for one-half hour and then added to a stirred suspension of 3 g copper sulfate, 90 ml of 12N hydrochloric acid and 62 ml of 40% sodium bisulfite. The resultant mixture was allowed to warm to room temperature and stirred for sixteen hours. It was then extracted with methylene chloride, the combined organic phases washed with water and saturated aqueous sodium chloride, dried over magnesium sulfate and added dropwise to 100 ml of methylene chloride containing 12.5 ml of liquified ammonia at -78°. This mixture was allowed to stir for two days at room temperature, then cooled to 0° and acidified with 10% hydrochloric acid. After separating the resultant two phases, the methylene chloride phase was washed with water and saturated sodium chloride followed by drying over magnesium sulfate and evaporation of the solvent to give 18.79 g of a solid melting at 145°-148°.

Workup

  1. temperatureThe grown mixture was cooled to 0°
  2. stirringstirred for sixteen hours
  3. extractionIt was then extracted with methylene chloride
  4. washthe combined organic phases washed with water and saturated aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. additionadded dropwise to 100 ml of methylene chloride containing 12.5 ml of liquified ammonia at -78°
  7. stirringto stir for two days at room temperature
  8. temperaturecooled to 0°
  9. customAfter separating the resultant two phases
  10. washthe methylene chloride phase was washed with water and saturated sodium chloride
  11. dry with materialby drying over magnesium sulfate and evaporation of the solvent

Sources & evidence

ORD record
ord-dfd0f13a254548d9859d9f6eb70a38f8
Source dataset
uspto-grants-1987_12
Patent number
USH0000386

Reaction notes

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